
Holiday rentals with beach access in Chicago Loop
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Top-rated rentals with beach access in Chicago Loop
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Apartment rentals with beach access

Andersonville's Secret Garden: 2 beds, 1 bath
Such a stylish and cozy spot in the heart of Andersonville! The beds were incredibly comfortable and the space had so much charm. Just steps away from great shops, restaurants, and everything else you would need near Clark street. Would definitely stay again!

Luxury Designer Penthouse|Private Deck|Gold Coast
Excellent place to stay. Quite a fe steps for those with issues getting up and down steps, but worth it.

Andersonville 2 bed with modern kitchen + bath
We had a truly wonderful stay at Mike and Lora’s place. The apartment is spacious, spotless, and very well-equipped. The beds are extremely comfortable, the linens were luxurious, the kitchen was a real treat to use, and the Wi-Fi worked perfectly throughout our stay. The location is amazing - right in the heart of the neighborhood, just steps away from great cafes and restaurants. It’s a super walkable area, which made it easy and enjoyable to explore everything on foot. Mike and Lora were responsive, thoughtful, and kind throughout our stay. Communication was smooth and easy, and we felt very well taken care of. Highly recommended - we’d love to come back someday!

Andersonville Living
We loved this cute, Craftman-style apartment. It was so homey and well arranged, nicely furnished, and beautifully decorated that we seriously wanted to move in! The owners were very thoughtful about providing what visitors will need. (They even provided a spare umbrella!) Everything was exactly as described, and communication was friendly and prompt. The only issue we had was trying to find on-street parking. We had to park several blocks away and, sadly, our car was stolen from that parking spot. Otherwise, it was a lovely neighborhood and a convenient location. Despite the parking problems, I would stay there again.

Andersonville Bicycle Studio
I had a wonderful stay at this lovely Airbnb! The decor was so thoughtful and definitely matched the bicycle studio vibes. The space was really cozy and welcoming. I especially appreciated the small details that showed how much care went into setting up the home. The host also left a kind handwritten note, which was such a warm and personal touch. It made me feel right at home from the moment I arrived. It was great being back in my old neighborhood for a visit and this space was in the perfect location. Highly recommend staying here!

NEW! |Studio Apartment Whiting IN, United States#2
Nice cozy play to stay, outside of the busy Chicago streets! Has good restaurants around that are walkable to.

Quiet city getaway by beach in fun neighborhood
Location is fantastic. Walking distance to beach, red line, buses, great food, shopping, etc. The apartment has a hip vibe and is located in a beautiful neighborhood that we really enjoyed walking through on our way in/out. Free dedicated parking is a huge bonus. Host was very responsive and you can tell they really care about the guest experience. Little things like packages of earplugs by the beds show how thoughtful they are. The neighborhood was pretty quiet most nights but it was nice to have the earplugs available.

Beautiful Hollywood-Ridge Suite in Edgewater
Dorothy was very welcoming and communicative, and the bagels and snacks were an extra nice touch. The rental is as described, if not better, and provided a quiet and comfortable place to stay. The location is well centered between Andersonville and the Bryn Mayr red line station with easy access to all of the locations in Edgewater. There is currently some road construction that blocks off close by roads, however, the streets are open to local traffic and it actually makes walking easier.
House rentals with beach access

Amazing historic campus mansion!
Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

House 5BED/3BATH/1PARKING close to Downtown & Lake
We would definitely use this location again when in town with family. Specious and only a short uber ride from everything we needed.

CasaNova Modern City Living
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Historic Old Town, Fabulous 4 Bedroom Home
We had the best stay in Old Town! The Airbnb was wonderful and spacious for our family.

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Words can’t describe how beautiful and clean the property and neighborhood is! The house is very spacious and modern. The basement is new, has a big room and bathroom with shower. The masters bedroom has a living room and GORGEOUS bathroom! The host provided cleaning supplies and even personal bathroom supplies for men and woman. The host was very nice and friendly 🥰 We had an incident with our previous AIRBNB and we had to rent this one last minute- The host responded at 1am letting us checked in at 1am. If you plan on staying here, please take care of it lol It’s such a lovely house! 100% Recommend!

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining
This was a fantastic find! My whole party loved the place. It was clean and wonderfully located in a peaceful neighborhood close enough to transport to walk but far enough from the noise and bustle of downtown. Shawn was very responsive to any questions I had and was super kind and friendly! I absolutely would stay here again!!

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.
Wow! I can’t say enough good things about Cheryl’s hosting! She and her husband went above and beyond for us. They are so responsive and friendly and even went so far as buying a pack and play for us last minute and jumping our car battery when it died! Talk about amazing! The place had everything we needed and the location was lovely. Would definitely stay here again!

Private Downtown Retreat with Rooftop Oasis
Our daughter was graduating from University of Chicago while our other daughter graduated from USAF flight school in Mississippi, and our family and friends visited from locations scattered around multiple time zones. Florin's location was simply the perfect place to handle such incoming chaos while lowering blood pressure to encourage a wonderful graduation experience headache-free. The rooftop experience was stunning, and everybody has been raving about the furnishings and easy-going environment in such a lovely place. The bathrooms and bedrooms were spa-worthy, and there were simply so many careful and thoughtful touches at this location that made it hard to leave! Florin has multiple parking options, but we only needed one nearby, offstreet parking place that was never a problem---surprising for a big city like Chicago! In short, this was probably the finest AirBnB we ever visited, and we are so grateful for such an exclamation point on a magical weekend. Thank you, Florin!
Apartment rentals with beach access

A Stones Throw from U Chicago South Campus!
Everything was great! The location was perfect—close to most of the attractions we visited during our stay. We really appreciated how well everything was set up. The honey was a lovely touch, and we especially enjoyed the peaceful, quiet atmosphere away from the city. Thank you for a wonderful experience!

Studio flat in the heart of Chicago's Gold Coast
everything was extremely nice, unfortunately the knob to change from shower to faucet was detached so we could not utilize the very large beautiful bathtub. The front porch light also needs to be replaced, we opted to leave the front door open to be able to see outside after dark. Other than that everything was extremely nice. Still worthy of a five-star review.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!

The Ramblers Inn, Northside NEW Reno w/parking!
Easy check in and close to LUC which is what we needed. Clean and comfortable. Bonus that it included parking.

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit
Chip and Lito's place is a dream! Spacious, clean, quiet, and convenient to restaurants, the "L", and the beach. Apartment is very well appointed, yet not cluttered. The shower is awesome! It was very nice to have a full kitchen, with coffee makers and dishwasher. I definitely plan to stay here the next time I visit Chicago!

Cozy 3BR on Chicago's North Side & Free Parking
Planned a weekend trip with our daughters and their partners to Chicago. Loved this location being outside of the city but very conveniently located to public transit. The house itself was beautiful and comfortable, with plenty of room for 6 adults. A perk was the driveway parking space for our car. Would definitely recommend to others and stay again when visiting Chicago!

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!

Andersonville: 3-bed, 2-bath w/ Dining RM & EZ PKG
Had an excellent time with my family at Ari’s place. It was very infant friendly and just as advertised. It’s easily walkable to the best places in Andersonville. We would stay here again!
Quick stats about holiday rentals with beach access in Chicago Loop
Total rentals
40 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
510 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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